2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-.omega.-phenyl-PGA1 or 9-deoxy-9,10-didehydro-PGD1 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,357,filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,055,602.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,055,602, issued Oct. 25, 1977.

I claim:
 1. A prostaglandin analog of the formula ##STR1## WHEREIN Z₃ isoxa or methylene; WHEREIN D is ##STR2## wherein Y is trans--CH═CH--;wherein M₁ is ##STR3## wherein R₅ is hydrogen or methyl; WHEREIN L₁ is##STR4## or a mixture of ##STR5## wherein R₃ and R₄ are hydrogen,methyl, or fluoro, being the same or different, with the proviso thatone of R₃ and R₄ is methyl only when the other is hydrogen ormethyl;Wherein g is one, 2, or 3; and Wherein s is zero, one, 2, or 3and T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbonatoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, thevarious T's being the same or different, with the proviso that not morethan two T's are other than alkyl.
 2. A compound according to claim 1,wherein D is ##STR6##
 3. A compound according to claim 2, wherein s iszero or one and T is chloro, fluoro, or trifluoromethyl.
 4. A compoundaccording to claim 3, wherein at least one of R₃ and R₄ is fluoro.
 5. Acompound according to claim 4, wherein R₃ and R₄ are both fluoro.
 6. Acompound according to claim 5, wherein R₅ is methyl. 7.2-Decarboxy-2-hydroxymethyl-15-methyl-16,16-difluoro-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-PGA₁,a compound according to claim
 6. 8. A compound according to claim 5,wherein R₅ is hydrogen. 9.2-Decarboxy-2-hydroxymethyl-16,16-difluoro-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁,a compound according to claim
 8. 10. A compound according to claim 3,wherein at least one of R₃ and R₄ is methyl.
 11. A compound according toclaim 10, wherein R₃ and R₄ are both methyl.
 12. A compound according toclaim 11, wherein R₅ is methyl. 13.2-Decarboxy-2-hydroxymethyl-15,16,16-trimethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁,a compound according to claim
 12. 14. A compound according to claim 11,wherein R₅ is hydrogen. 15.2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁,a compound according to claim
 14. 16. A compound according to claim 3,wherein R₃ and R₄ are both hydrogen.
 17. A compound according to claim16, wherein R₅ is methyl. 18.2-Decarboxy-2-hydroxymethyl-15-methyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁,a compound according to claim
 17. 19. A compound according to claim 16,wherein R₅ is hydrogen. 20.2-Decarboxy-2-hydroxymethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁,a compound according to claim
 19. 21. A compound according to claim 20,wherein D is ##STR7##
 22. A compound according to claim 21, wherein s iszero or one and T is chloro, fluoro, or trifluoromethyl.
 23. A compoundaccording to claim 22, wherein at least one of R₃ and R₄ is fluoro. 24.A compound according to claim 23, wherein R₃ and R₄ are both fluoro. 25.A compound according to claim 24, wherein R₅ is methyl. 26.2-Decarboxy-2-hydroxymethyl-16,16-difluoro-17-difluoro-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-9-deoxy-9,10-didehydro-PGD.sub.1,a compound according to claim
 25. 27. A compound according to claim 24,wherein R₅ is hydrogen. 28.2-Decarboxy-2-hydroxymethyl-16,16-difluoro-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 27. 29. A compound according to claim 22,wherein at least one of R₃ and R₄ is methyl.
 30. A compound according toclaim 29, wherein R₃ and R₄ are both methyl.
 31. A compound according toclaim 30, wherein R₅ is methyl. 32.2-Decarboxy-2-hydroxymethyl-15,16,16-trimethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD.sub.1,a compound according to claim
 31. 33. A compound according to claim 30,wherein R₅ is hydrogen. 34.2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 33. 35. A compound according to claim 22,wherein R₃ and R₄ are both hydrogen.
 36. A compound according to claim35, wherein R₅ is methyl. 37.2-Decarboxy-2-hydroxymethyl-15-methyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 36. 38. A compound according to claim 35,wherein R₅ is hydrogen. 39.2-Decarboxy-2-hydroxymethyl-17-phenyl-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim 38.